


Heartache and Confessions

by jelly123



Category: Supernatural
Genre: Break Up, Challenge Response, Challenges, Cross-Posted on Tumblr, Cute Ending, Dickish Boyfriend, F/M, Fluffy Ending, Reader-Insert, Sad, Sweet Dean Winchester
Language: English
Status: Completed
Published: 2017-05-11
Updated: 2017-05-11
Packaged: 2018-10-30 18:02:52
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,178
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10882089
Author URL: https://archiveofourown.org/users/jelly123/pseuds/jelly123
Summary: Life had seemed like it was going great, hunting with the Winchesters, killing evil sons of bitches. Hanging out with your boyfriend Josh and balancing hunter and normal person.





	Heartache and Confessions

**Author's Note:**

> What’s this? Another fic challenge completed?? (I promise I’m working on everything else, just I’ve fallen into the Dean/Jensen trash pile again and this is(n’t) helping) This was written for @klaineaholic 400 Follower Fics challenge, congrats Kiri on the milestone! (I have my quote bolded so it stands out)

“And where are you going?” Dean asked, looking up from his laptop.

“Out. It’s date night.” I said, placing a hand on my hip.

“We just got back and you’re already heading out?”

“Yes. Some of us actually have lives outside of hunting.” I rolled my eyes, preparing for the fight that was about to break out, “Just because some of us are happy living with random hookups, doesn’t mean all of us are. Josh is hot, and he understands, and I don’t even know why I’m explaining this to you, you don’t really care.”

“Nope. Not one bit.” He said turning back to whatever he was doing, “Have fun.”

“Damn right, I’m going to have fun. Going to have an awesome night, with my awesome boyfriend.” I grumbled under my breath, stomping my feet like a child all the way up the stairs.

Dean just doesn’t get it. Some of us had normal lives before we started hunting, there is a way to balance the two. Especially now that I actually have somewhere to live, and I don’t have to jump around place to place. If he just met Josh, he would understand. I mean, what we have is somewhat casual, but at the same time, we only ever see each other. He waits for me to come home, and vise versa.

By the time I reached Josh’s house, I had severely calmed down from my confrontation with the oldest Winchester. I was excited, butterflies dancing in my stomach as I walked up his front steps.

“Oh. Y/n. You’re here.” Josh said as he opened the door.

“I said I was coming home today. I know we didn’t have anything planned, but I just wanted to spend time with you.” I smiled, walking past him.

“Um. Now’s not really a great time. I just got off work and I don’t really feel like going out.” He said.

“That’s fine. We don’t have to go out. We can stay in, order take out, curl up on the couch and watch a movie.” I shrugged.

“Actually,” Josh scratched the back of his neck, “I had something I was meaning to talk to you about.”

“What’s up Babe?”

“Look, I think you’re super cool and fun to hang around,”

“There’s a but coming. Just spit it out.” I knew where this conversation was heading.

“But, you’re never around. You’re always leaving State, ‘for work’, and you never tell me what that ‘work’ is. I dunno if I can handle the sometimes girlfriend anymore.”

“Can’t say I didn’t see this coming.” _Bullshit! Why are you taking the high road here?!_ “Got any clichéd break up lines for me? Like it’s not you, it’s me? Or; I met someone else?”

“Well.”

“You actually met someone else.” I sighed, “How long?”

“I’ve been seeing her a few weeks.”

“Wow. It’s taken you that long to have the balls to break up with me. Just wow Josh. She know about me? She know about last weekend? Probably not.”

“Y/n, I’m sorry. I wanted to say something that night, but you came over and then we-”

“We fucked. You can say it, you were going to dump my sorry ass, but thought, ‘hey if she’s opening, might as well’. I can’t believe you.” I turned on my heel, “Have a nice life Josh.”

I made it all the way to my car before I broke down. All the emotion of the last twenty minutes finally breaking through the wall I had placed.

_Who does Josh think he is_? He’s a coward, he waited weeks to dump me, and for what? Maybe Dean was right, hunters can’t do normal relationships. I should have listened to him. God, I must be upset if I’m thinking Dean was right.

Wiping my eyes, I finally started my car and headed home. I was determined not to let the boys know I was crying; they didn’t need to see that. I’ll just casually walk through the bunker, grab the tub of ice cream, and a bottle of scotch and hole up in my room for the next day.

_It won’t be so bad, what I had with Josh, it was nice, but it wasn’t meant to last._ Ugh, why am I trying to talk myself out of this? I was hoping with him; he could have been the long haul. I could have told him what I do, maybe move in and settle down. But now, I get to probably die alone.

Thankfully, the drive between Josh’s and the bunker is only ten minutes. I don’t think I can hold out much longer. I can feel the tears building back up, and I want nothing more than to curl up in my bed.

Walking down the stairs, it seems that neither brother is around, probably off in their rooms, or whatever.

“Y/n?” _Crap. Where did he come from?_

“Yeah, Dean?”

“You’re home early. Everything okay?” He asked, coming out of the kitchen.

“Yeah. I’m fine. Josh was tired from work, didn’t feel like hanging out tonight.” I lied.

“Oh. Okay. Well, I was going to watch that cartoon you wanted me to watch, ugh, Stewart Galaxy?”

“Steven Universe. Just let me get changed, and I’ll come watch it with you.” I said.

“Cool. Meet me in my room. I have my laptop set up.”

Five minutes later, I was changed and settling in on Dean’s bed. He handed me a beer as he sat beside me, and I looked up at him questioningly. Usually if we watched TV or a movie in his room, food and drink were not allowed.

“You looked like you could use it,” He shrugged, “Just this once I’ll let it slide.”

“Thank you.” I muttered, lifting it to my mouth and taking a long pull from it.

He shifted so that his legs were lying out in front of him and his laptop was resting on them, I scooted closer when he pressed play. It didn’t feel like it took very long to get through the entire first season, (doesn’t help that each episode is only like eleven minutes long). By the time we finished, I had my head resting on his shoulder, quietly singing along to the theme song at the start of each new episode.

“You going to tell me what really happened tonight?” He asked quietly.

“Leave it to you to see past my bullshit.” I sighed, “He dumped me.”

“Why?”

“He met someone else, and he was tired of waiting around for me.” I could feel the tears start to build back up.

“I thought you said he understood?” Dean asked.

“I thought he did, but apparently I was wrong.”

“For what’s it worth, I never thought much of him. The way you talk about him, it didn’t seem like he ever intended for what you had to be any more than that.”

“Thanks Dean, because that made me feel so much _better_.” I rolled my eyes at him.

“It’s the truth Sweetheart. **You said you were always trying to make him happy. Did he even know he was making you sad?”**

“He wasn’t making me sad. What are you talking about Dean?” I scrunched my nose in confusion.

“I’m saying; every time you came back from hanging out with him, you were a different person, something about you had changed. At first I thought nothing of it, then as it went on, I noticed it more and more. You weren’t happy with him; you were just trying to make it work. I bet you wanted it to work out so bad, that you didn’t care that to him you were just a booty call. Don’t give me that look Y/N/N, just think about it. You’ve been a different person the last few months, and for what?”

“Holy shit.” I whispered, mulling Dean’s words around in my head. Sometimes it’s easy to forget how observant Dean actually is.

“He didn’t deserve someone like you. You’re amazing Y/N, you’re smart and beautiful and overly passionate about silly cartoons. A badass hunter who doesn’t take shit from anybody. You’re the first person, besides Sam, that I’d choose to have my back in any situation. I can’t imagine anyone less deserving of your time and attention than that loser.”

Sometimes it was hard to read Dean, other times you could read him like a book. This was not one of those times. He was being sweet and supportive, everything a friend should be, but at the same time, his words held a meaning behind them. The expression on his face was open, waiting patiently for me to think about what he said and respond.

“But this life doesn’t leave me with a lot of options. Other decent hunters are few and far between, someone who doesn’t know seems like the best way to go.” I said.

“But what about the options regarding that civilian? Do you lie to them the rest of your life, just one day never coming home, leaving them wonder what happened to you? Or do you tell them what you do and hope they don’t throw you in an asylum? Neither one sounds pleasant.”

“Or, I’ll just die alone.” I threw my hands up in the air, not even sure where this was heading anymore.

“You’re not dying alone, Y/N/N. Now you’re just being dramatic.” He laughed, “There’s someone, somewhere out there that will appreciate and love every part of you.”

“You sound so sure of that.” I rolled my eyes.

“Maybe I’m talking from experience.” He shrugged, “Maybe, for once you’ll listen to me and stop beating yourself up over some douche.”

“Yeah, okay.” I was slightly uncomfortable with the turn of the conversation, this wasn’t like the Dean I know, this was way too sappy for his liking. I didn’t want to think about the why behind it all, that opens another can of worms, and I’m not sure I want to open it. Or do I? Ugh, the emotional roller coaster of this whole night has my head swimming.

On the one hand, it would be so easy, falling in love with Dean Winchester. He’s a hunter, he wouldn’t be wondering where I was half the time, he’d be right beside me. We already spend 85% of our time together, it wouldn’t be that far of a stretch.

But on the other hand; it’d get complicated. Every bad thing in the world would try and use the other as an advantage, it would put our lives at risk more so than they already are. We’re both stubborn and pigheaded. I pick a fight with him, just for the sake of boredom sometimes.

But, there’s always a but. The pros and cons never are balanced when you sit down and actually think about them. That’s not what you’re supposed to do, it shouldn’t be about convenience or settling for something because it’s easy. It should be messy; a whirlwind of emotions constantly.

“You coming back to me anytime, Princess?” Dean asked waving a hand in front of my face.

“I didn’t even realize I spaced out.” I shook my head.

“It’s alright. What were you thinking about?”

“Just what you said.” _And what you didn’t say._

“Care to share with the rest of the class?” His lip curled up at the end.

“Life with a hunter would be so easy, yet so fucking complicated all at the same time.” I flopped back onto his pillows, opting to stare at the ceiling, “There wouldn’t be any secrets, or very few if there were. But the targets on our backs, would double in size. For every good thing about being with a hunter, there’s something bad too. It just makes sense and it doesn’t.”

“But if it was easy, wouldn’t it get boring?”

“Yeah.” I said, turning my head to face him. He had moved so he was laying beside me, those green eyes watching me as I voiced my thoughts, “At first boring wouldn’t be so bad, there’d be a routine to everything. But it wouldn’t make me happy- it didn’t make me happy.”

He nodded in agreement, knowing that I finally understood what he was saying in the first place. Everything with Josh had actually become a routine, we’d hang out at his place, or go out to dinner then go back to his place. It was the same thing day after day, nothing changed; except me. I was trying to force myself into loving him. That he was the best I could do, given my circumstances.

“Why has it taken me this long to figure out?” I asked.

“I think you’ve known all along, you’ve just been too stubborn to figure it out.” He laughed, hand brushing against mine.

“Thank you Dean.” I said as I intertwined my finger with his.

“For what?”

“For reminding me that I’m better than whatever Josh thought of me.” I closed my eyes, giving his hand a gentle squeeze.

“Anytime, Y/N, anytime.”


End file.
